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258 Cross Street, Winchester MA 01890

Winchester, MA 01890
$699,000
Est. $4,360/month
4
Beds
2
Baths
1,719
Sq Ft
$407
Price/Sq Ft
0.18
Acres
1860
Year Built
165
Days on Market
Closed Listed Oct 25, 2019 • MLS# 72585005 Copied!

About this home

AMAZING PRICE for this home with expansion potential located on the corner of River Street with huge yard, driveway access on the side road...Move right in and enjoy this quaint home with high ceilings and spacious rooms! Situated nicely on a large corner lot with great expansion potential! Sunny kitchen formal dining room, living room with original detail , large master, second floor laundry finished third floor With 2 more rooms - home is in great condition and awaiting its new owners! Easy access to downtown shopping and schools - please call for a private viewing!

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Public Records

Current Owner

Owner CONNORS GRAYSON + KATHERINE BOOK
Mailing Address 258 CROSS ST, WINCHESTER, MA, 1890

Land Use

Use Code 101
Description Single Family
Zoning RG
Style OLD STYLE

Tax Information

Assessed Value $865,700

Assessment History

Year Land Building Total Change
FY2026 $533,600 $332,100 $865,700

Sale History

Date Price Book/Page
Jun 1, 2020 $699,000 74794/447

Building Permit History

Permit history not yet available for this municipality.

Municipal Context: WINCHESTER

Match: geocode_proximity (89.7% confidence) · Data as of Jun 1, 2026

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1860
Bedrooms
4
Full Bathrooms
2
Living Area
1,719 sq ft
Total Rooms
7

Sale Statistics

Sale Overview
Original List Price: $745,000
Final Sale Price: $699,000
Difference: $46,000 (-6.2%)
Performance Metrics
93.8%
List to Sale Ratio
Sold below asking price
165
Days on Market
Extended listing
Price per Square Foot Analysis
Original $/sq ft: $433
Sale $/sq ft: $407
This property sold for $407 per square foot
Sale Summary

This property sold for 6.2% below the original asking price.

At 165 days on market, this property took longer than average to sell.

Nearby Sales Comparison

Based on 3 similar properties sold within 0.5 miles in the last 90 days

This Property
$407/sq ft
Area Average
$602/sq ft
Difference
32.4%

This property sold below the area average, potentially representing good value for the buyer.

Facts & Features

Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 1860
Living Area 1,719 sq ft
Lot Size 0.18 acres
Bedrooms 4
Full Baths 2
Total Rooms 7

Interior

Heating Forced Air, Natural Gas
Cooling Central Air
Flooring Wood, Carpet
Appliances Gas Water Heater, Range, Dishwasher, Disposal, Washer, Dryer
Fireplace None
Basement Unfinished
Laundry Second Floor
Features Mud Room

Exterior

Construction Frame
Architecture Colonial
Roof Shingle
Features Fenced Yard
Pool None
Spa None
Fencing Fenced
Patio/Porch None

Parking

Features Off Street, Driveway
Total Spaces 4

Utilities

Electric Circuit Breakers
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax $7,508
Assessed Value $620,000

Interior Features

Flooring: Wood, Carpet
Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Washer, Dryer
Interior Features: Mud Room
Windows: Insulated Windows
Basement: Unfinished
Laundry: Second Floor
Security:

Construction & Materials

Style: Colonial
Year Built: 1860
Structure Type:
Exterior Materials: Frame
Roof: Shingle
Foundation: Stone

Heating, Cooling & Utilities

Heating: Forced Air, Natural Gas
Heating Zones: 1
Cooling: Central Air
Cooling Zones: 1
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Fenced Yard
Patio & Porch:
Fencing: Fenced
Other Structures:
Lot Features: Corner Lot
Road Surface:

Parking & Garage

Total Parking Spaces: 4
Parking Features: Off Street, Driveway

Location

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Neighborhood

258 Cross Street, Winchester MA 01890

Winchester, MA 01890

Walkability

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Nearby Schools

School District
Winchester School District local
A+
School Safety 2024-25
0.1% Very Low (Safest)
0.1% Suspensions 0.1% In-School
5.4% below state avg
E

Elementary Schools

10 schools
Acera School
0.2 mi
Grades K-08
The Wilder School
0.5 mi
Grades K-12
A+
Muraco Elementary School
0.3 mi | #62 of 824 | Score: 61.6
Improved 62 spots from last year
+3.4 above state avg
352 students Diverse
Rising School Strong Attendance
Grades K-05
Creative Corner School Inc
0.5 mi
Grades PK-K
A
Lynch Elementary School
0.8 mi | #113 of 824 | Score: 58.6
Dropped 31 spots from last year
+0.4 above state avg
426 students Diverse
Grades PK-05
St. Mary Elementary School
0.8 mi
Grades PK-05
A+
Lincoln Elementary School
1.0 mi | #74 of 824 | Score: 60.7
Dropped 29 spots from last year
+2.5 above state avg
334 students Moderate
Strong Attendance
Grades K-05
A+
Ambrose Elementary School
1.7 mi | #11 of 824 | Score: 66.1
Improved 36 spots from last year
+7.9 above state avg
398 students Moderate
Rising School Strong Attendance
Grades K-05
Children's Own School
1.9 mi
Grades PK-K
A+
Vinson-Owen Elementary School
2.2 mi | #40 of 824 | Score: 63.2
Improved 112 spots from last year
+5 above state avg
441 students Diverse
Rising School Strong Attendance
Grades PK-05
M

Middle Schools

1 school
A+
McCall Middle School
1.1 mi | #16 of 352 | Score: 62.4
Dropped 3 spots from last year
+4.2 above state avg
1,036 students Diverse
Strong Attendance
Grades 06-08
H

High Schools

1 school
A+
Winchester High School
0.7 mi | #17 of 346 | Score: 73.6
Improved 18 spots from last year
+15.4 above state avg
1,404 students Diverse
20 sports • 2,818 athletes
Strong AP Program High Graduation Rate College Ready Curriculum Strong Athletics
Grades 09-12
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Monthly Payment Calculator

Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%

Monthly Payment Breakdown

Principal & Interest $0
Property Tax $626
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo

Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Market Insights

39.2%
Price Range
167
Total Days on Market
1
Previous Sales

Property Timeline

Current Active Listing - MLS #73541288
Full transaction history available when tracking began
🏡
Currently Listed
Jun 24, 2026
$999,900
MLS #73541288 - Active
Sold
Jun 1, 2020
$699,000
Property sold
Days on Market: 167
🏠
Listed for Sale
Oct 25, 2019
$699,000
Original listing
Agent: Kim Covino Office: Leading Edge Real Estate
Previous Transaction - MLS #72380664
Full transaction history available when tracking began
🏷️
Previously Sold
Jan 25, 2019
$607,500
MLS #72380664

Price & Status History

Date Event Price Change
Jun 25, 2026 Sold $999,900
Oct 25, 2019 New Listing Added $699,000
Jan 25, 2019 Sold $607,500

Market Statistics

Days on Market
165 days
Price per Sq Ft
$407

Tax History

Year Taxes Assessment
2019 $7,508 $620,000

Financial Details

Annual Property Tax
$7,508
Tax Year 2019
Assessed Value
$620,000

Listing Information

Listing Office Leading Edge Real Estate
Agent MLS ID BB801821
Office MLS ID AN4643
Listing Data Updated Jun 1, 2020 3:29 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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Market Analytics for Winchester, MA

Real-time market trends and pricing data for this area

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